In 1962, at the height of his fame, Frank Sinatra gave a benefit performance at the behest of a British princess. He gave another for the head of the Chicago mob.
In February, he sang at a ritzy London fundraiser for a children's charity favored by Princess Margaret. Later that year, he did a week's gig at the Villa Venice, a gaudy but financially ailing nightclub near Northbrook in which mafioso Sam Giancana had a piece of the action.
Will Leonard, the Tribune's nightlife critic, reported that Sinatra and his pals, Dean Martin and Sammy Davis Jr., "croon, carol, caper and clown to the biggest cabaret audiences this town has seen in years." And no wonder.
Gossip columnists had bestowed the honorific "Chairman of the Board" on Sinatra, whose 100th birthday on Dec. 12 is opening a floodgate of nostalgia. Giancana was the flamboyant face of the Chicago Outfit. The linking of the two luminaries turned those seven days in November and December into a requiem for an older show-biz era.
Chicago's entertainment scene was changing. Comedian Lenny Bruce had brought his obscenity-leavened act to the Gate of Horn, a hip club where the Chad Mitchell Trio also appeared. Their kind of folk music was already sufficiently popular for the Smothers Brothers to satirize it at the State-Lake Theater. The Rat Pack, Sinatra and his friends, were strictly old-school but still a magnetic draw to nightlife veterans of a time when Rush Street was home to celebrated nightclubs, not dating bars.
"The old Chez Paree crowd has yanked itself loose from the TV sets just once more," Leonard observed in another account of the goings-on at the Villa Venice. "The old waiters and doormen are back, showing the same old palms of the same old hands. There's a great big band on the stand, playing great big music. The chairs are pushed so closely together you can't shove your way between them. Flash bulbs pop in the audience during the show. All that's missing is the girl selling the Kewpie dolls and giant sized postcards."
Herb Lyon, the Trib's gossip columnist, proclaimed the hordes of screaming fans "Madness at the Villa." He quoted Sinatra and his buddies (or perhaps their publicist) as saying: "We've never seen anything like it anywhere — Vegas, New York, Paris, you name it."
Indeed, the Villa Venice had been tricked out in a style imported from Las Vegas. Giancana reportedly spent upward of $250,000 to restore it and its canals plied by gondolas. The showroom seated 800, was furnished with satin ceilings, tapestries, and statuesque, lightly clothed showgirls. Nearby was the ultimate accouterment of a Vegas-like operation: a gambling casino in a Quonset hut a few blocks from the Villa. High rollers were whisked between the supper club and the dice and roulette tables in a shuttle supervised by Sam "Slick" Rosa, identified by the Trib as "the syndicate's chief of limousine service," and his assistant, Joseph "Joe Yak" Yacullo.
The Tribune reported that among the mobsters on hand for Sinatra's opening night were Willie "Potatoes" Daddano, Marshall Caifano, Jimmy "The Monk" Allegretti and Felix "Milwaukee Phil" Alderisio. It was noted that "Sinatra's gangland fans from other cities appeared too." For a week, the Rat Pack's presence turned Milwaukee Avenue at the Des Plaines River into the hottest address in show biz.
Shortly before the Sinatra show closed, the casino shut down under belated pressure from law enforcement authorities who told the Tribune that the gambling operation had grossed $200,000 in two weeks. That threw a monkey wrench into Giancana's business plan, which depended on recouping his investment by attracting gamblers with a parade of big-name acts. But how could he hope to book stars like Sinatra and his buddies into a scarcely known venue in the hinterlands of Chicago? What kind of money did he dangle in front of them? Wondering if there might have been a nonmonetary enticement, the FBI interviewed the Rat Pack during their engagement. Perhaps the feds took a clue from Dean Martin's rewording of the old standard "The Lady is a Tramp":
I love Chicago, it's carefree and gay
I'd even work here without any pay.
According to James Kaplan, author of the recently published "Sinatra: The Chairman," the question was put to Davis. "I got one eye, and that one eye sees a lot of things that my brain tells me I shouldn't talk about," Davis told the agents. "Because my brain says that, if I do, my one eye might not be seeing anything after a while."
Kaplan's verdict was that it was unclear whether the Rat Pack got paid. As a favor to Giancana, Sinatra had previously persuaded a reluctant Eddie Fisher to play the Villa Venice, reportedly for chicken feed. Sinatra owed Giancana for lending his muscle in the critical state of West Virginia when John F. Kennedy ran for president in 1960, according to Giancana's daughter Antoinette's memoir "Mafia Princess: Growing Up in Sam Giancana's Family."
Still, the Rat Pack's Villa Venice appearances were wildly successful, as the Tribune's Lyon reported: "It is now estimated that the total Villa loot for the seven-day Sinatra-Martin-Davis run will hit $275,000 to $300,000, a new night club record." But Dinah Shore, the next scheduled performer, canceled at the last minute, and Sheilah Graham, a nationally syndicated columnist, wrote: "I've been told that Sinatra picked up the hotel tab for his group, to the tune of $5,000. The whole business sounds somewhat odd."
In fact, the Villa Venice never again hosted big-name stars, operating thereafter as a catering hall, with a new management taking over in 1965. Two years later, it was destroyed by a spectacular, if mysterious, fire. The spot is now a Hilton hotel.
Giancana was gunned down in his Oak Park home in 1975.
To the end of Sinatra's days, he sang the Windy City's praises. But fellow Rat Packer Peter Lawford reportedly said the song was an encomium not to the city but to Giancana, calling the song "his tribute to Sam, an awful guy with a gargoyle face and weasel nose."
Either way, "Chicago" was Sinatra's theme song:
I saw a man and he danced with his wife in Chicago
Chicago, Chicago that's my hometown.
Thanks to Ron Grossman.
Best of the Month!
- Top 10 Most Wanted True-Crime Movies
- Chicago Mob Infamous Locations Map
- The Brothershood Mob Squad
- Teacher has Sex with Students, Then Threatens them with the Mafia
- The Chicago Syndicate AKA "The Outfit"
- Profile: Harry Aleman
- Protected Witness, Sal Romano, Testifies at Mob Trial
- Mafia Links of Frankie Valli and the Four Seasons
- Firm with reputed mob ties flourishes
- Legendary Don: Mysterious and powerful, Joe Bonanno Retreated to Tucson, but Violence Followed